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Preparation and properties of self-healing tung oil-based polymer networks driven by thermo-reversible Diels–Alder reaction

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Abstract

Mixtures of tung oil (TO) and 4,4’-bismaleimidodiphenylmethane (BMI) in the molar ratios of 1:3 and 2:3 were cured at 100 °C or 160 °C to produce the cured products (TB13, TB23 or htTB13, htTB23). Fourier-transform infrared spectroscopy of the cured products confirmed that the trans, trans-diene moieties of TO are almost completely consumed for all the cured products; furthermore, the maleimide groups were almost completely consumed for all the cured products, except for TB13. Differential scanning calorimetry results of the cured products revealed that TB13 and TB23 exhibited strong endothermic peaks due to the retro-Diels–Alder (rDA) reaction. The rDA enthalpy change (ΔHrDA) of TB13 was higher than that of TB23, and the ΔHrDAs of htTB13 and htTB23 were considerably smaller than that of TB13 and TB23. The tan δ peak temperatures of the cured products measured by dynamic mechanical analysis were in the range of 55–131 °C and were increased in the order: TB23 < TB13 < htTB23 < htTB13. The 5% weight loss temperatures of all the cured products were higher than 400 °C. Although TB13 and TB23 exhibited self-healing properties upon hot-pressing at 100 and 120 °C, respectively, htTB13 and htTB23 exhibited no self-healing ability.

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References

  1. Guo Q (2012) Thermosets: Structure, Properties, and Applications, 2nd edn. Elsevier, Amsterdam

    Book  Google Scholar 

  2. Kutuzova L, Kandelbauer A (2022) In: Dodiuk H (ed) Handbook of Thermoset Plastics, 4th edn. Elsevier, Amsterdam

    Google Scholar 

  3. Urdl K, Kandelbauer A, Kern W, Müller U, Thebault M, Zikulnig-Rusch E (2017) Self-healing of densely crosslinked thermoset polymers—a critical review. Prog Org Coat 104:232–249. https://doi.org/10.1016/j.porgcoat.2016.11.010

    Article  CAS  Google Scholar 

  4. Longo P, Mariconda A, Calabrese E, Raimondo M, Naddeo C, Vertuccio L, Russo S, Iannuzzo G, Guadango L (2017) Development of a new stable ruthenium initiator suitably designed for self-repairing applications in high reactive environments. J Ind Eng Chem 54:234–251. https://doi.org/10.1016/j.jiec.2017.05.038

    Article  CAS  Google Scholar 

  5. Hayes SA, Jones FR, Marshiya K, Zhang W (2007) A self-healing thermosetting composite material. Compos A 38:1116–1120. https://doi.org/10.1016/j.compositesa.2006.06.008

    Article  CAS  Google Scholar 

  6. Guadango L, Vertuccio L, Naddeo C, Calabrese E, Barra G, Raimondo M, Sorrentino A, Binder WH, Michael P, Ranna S (2019) Self-healing epoxy nanocomposites via reversible hydrogen bonding. Compos B 157:1–13. https://doi.org/10.1016/j.compositesb.2018.08.082

    Article  CAS  Google Scholar 

  7. Paolillo S, Bose RK, Santana MH, Grande AM (2021) Intrinsic self-healing epoxies in polymer matrix composites (PMCs) for aerospace applications. Polymers 13:201. https://doi.org/10.3390/polym13020201

    Article  CAS  PubMed Central  Google Scholar 

  8. Guadagno L, Vertuccio L, Naddeo C, Calabrese E, Barra G, Raimondo M, Sorrentino A, Binder WH, Michael P, Rana S (2019) Reversible self-healing carbon-based nanocomposites for structural applications. Polymers 11:903. https://doi.org/10.3390/polym11050903

    Article  CAS  PubMed Central  Google Scholar 

  9. Wang X, Xu J, Zhag Y, Wang T, Wang Q, Yang Z, Zhang X (2022) High-strength, high-toughness, self-healing thermosetting shape memory polyurethane enabled by dual dynamic covalent bonds. Polym Chem 11:3422. https://doi.org/10.1039/d2py00564f

    Article  CAS  Google Scholar 

  10. Karami Z, Zolghadr M, Zohuriaan-Mehr MJ (2020). In: Thomas S, Surendran A (eds) Self-healing Polymer-Based Systems. Elsevier, Amsterdam

    Google Scholar 

  11. Pratama PA, Sharifi M, Peterson AM, Palmese GR (2013) Room temperature self-healing thermoset based on the Diels−Alder Reaction. ACS Appl Mater Interfaces 5:12425–21243. https://doi.org/10.1021/am403459e

    Article  CAS  PubMed  Google Scholar 

  12. Liu YL, Chuo TW (2013) Self-healing polymers based on thermally reversible Diels-Alder chemistry. Polym Chem 4:2194–2205. https://doi.org/10.1039/c2py20957h

    Article  CAS  Google Scholar 

  13. Yasuda K, Sugane K, Shibata M (2020) Self-healing high-performance thermosets utilizing the furan/maleimide Diels-Alder and amine/maleimide Michael reactions. J Polym Res 27:18. https://doi.org/10.1007/s10965-019-1986-z

    Article  CAS  Google Scholar 

  14. Zolghadr M, Shakeri A, Zohuriaan-Mehr MJ, Salimi A (2019) Self-healing semi-IPN materials from epoxy resin by solvent-free furan-maleimide Diels-Alder polymerization. J Appl Polym Sci 136:48015. https://doi.org/10.1002/app.48015

    Article  CAS  Google Scholar 

  15. Dotan A (2014) In: Dodiuk H, Goodman SH (eds) Handbook of Thermoset Plastics, 3rd edn. Elsevier, Amsterdam

    Google Scholar 

  16. Auvergne R, Caillol S, David G, Boutevin B, Pascault JP (2013) Pascault, Biobased thermosetting epoxy: Present and future. Chem Rev 114:1082–1115. https://doi.org/10.1021/cr3001274

    Article  CAS  PubMed  Google Scholar 

  17. Liu J, Zhang L, Shun W, Dai J, Peng Y, Liu X (2021) Recent development on bio-based thermosetting resins. J Polym Sci 59:1474–1490. https://doi.org/10.1002/pol.20210328

    Article  CAS  Google Scholar 

  18. Bobade SK, Paluvai R, Mohanty S, Nayak SK (2016) Bio-based thermosetting resins for future generation: A review. Polym Plast Technol Eng 55:1863–1896. https://doi.org/10.1080/03602559.2016.1185624

    Article  CAS  Google Scholar 

  19. Mustapha SNH, Rahmat AR, Arsad A (2014) Bio-based thermoset nanocomposite derived from vegetable oil: a short review. Rev Chem Eng 30:167–182. https://doi.org/10.1515/revce-2013-0010

    Article  CAS  Google Scholar 

  20. Galià M, Espinosa LM, Ronda JC, Lligadas G, Cádiz V (2010) Vegetable oil-based thermosetting polymers. Eur J Lipid Sci 112:87–96. https://doi.org/10.1002/ejlt.200900096

    Article  CAS  Google Scholar 

  21. Hirayama K, Irie T, Teramoto N, Shibata M (2009) High performance bio-based thermosetting resins composed of dehydrated castor oil and bismaleimide. J Appl Polym Sci 114:1033–1039. https://doi.org/10.1002/app.30562

    Article  CAS  Google Scholar 

  22. Stenzenberger HD (1994) In: Hergenrother PM (ed) High performance polymers (Advances in polymer science, Vol. 117) Springer, Berlin

  23. Stenzenberger H (1988) Recent advances in thermosetting polyimides. Br Polym J 20:383–396

    Article  CAS  Google Scholar 

  24. Canning MS, Stenzenberger H (1986) Compimide bismaleimide resins – high performance thermosetting systems. Mater Des 7:207–211. https://doi.org/10.1016/0261-3069(86)90128-7

    Article  Google Scholar 

  25. Nair CPR (2004) Advances in addition-cure phenolic resins. Prog Polym Sci 29:401–498. https://doi.org/10.1016/j.progpolymsci.2004.01.004

    Article  CAS  Google Scholar 

  26. Guo Y, Han Y, Liu F, Zhou H, Chen F, Zhan T (2015) Fluorinated bismaleimide resin with good processability, high toughness, and outstanding dielectric properties. J Appl Polym Sci. https://doi.org/10.1002/app.42791

    Article  Google Scholar 

  27. Shibata M, Teramoto N, Nakamura Y (2011) High performance bio-based thermosetting resins composed of tung oil and bismaleimide. J Appl Poly Sci 119:896–901. https://doi.org/10.1002/app.32770

    Article  CAS  Google Scholar 

  28. Harwood JL, Woodfield HK, Chen G, Weselake R (2017) In: Ahmad M (ed) Fatty Acids, 1st edn. Elsevier, Amsterdam

    Google Scholar 

  29. Biermann U, Butte W, Eren T, Haase D, Metzger JO (2007) Regio- and stereoselective Diels-Alder additions of maleic anhydride to conjugated triene fatty acid esters. Eur J Org Chem 23:3859–3862. https://doi.org/10.1002/ejoc.200700243

    Article  CAS  Google Scholar 

  30. Lacerda TM, Carvalho AJF, Gandini A (2014) Two alternative approaches to the Diels-Alder polymerization of tung oil. RSC Adv 4:26829. https://doi.org/10.1039/c4ra03416c

    Article  CAS  Google Scholar 

  31. Lee HS, Lee SM, Park SL, Choi TR, Song HS, Kim HJ, Bhatia SK, Gurav R, Kim YG, Kim JH, Choi KY, Yang YH (2021) Tung oil-based production of high 3-hydroxyhexanoate-containing terpolymer poly(3-hydroxybutyrate-co-3-hydroxyvalerate-co-3-hydroxy-hexanoate) using engineered Ralstonia eutropha. Polymers 13:1084. https://doi.org/10.3390/polym13071084

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  32. Bhattacharyya AS, Kumar S, Sharma A, Kumar D, Patel SB, Paul D, Dutta PP, Bhattacharjee G (2017) Metallization and APPJ treatment of bismaleimide. High Perform Polym 29:816–826

    Article  CAS  Google Scholar 

  33. Schönemann A, Edwards HGM (2011) Raman and FTIR microspectroscopic study of the alteration of Chinese tung oil and related drying oils during ageing. Anal Bioanal Chem 400:1173–1180. https://doi.org/10.1007/s00216-011-4855-0

    Article  CAS  PubMed  Google Scholar 

  34. Gearing J, Malik KP, Matejtschuk P (2010) Use of dynamic mechanical analysis (DMA) to determine critical transition temperatures in frozen biomaterials intended for lyophilization. Crybiology 61:27–32. https://doi.org/10.1016/j.cryobiol.2010.04.002

    Article  CAS  Google Scholar 

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Acknowledgements

We thank Dr. Naozumi Teramoto of our department for his helpful suggestions.

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The authors declare that no funds, grants, or other support were received during the preparation of this manuscript.

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  1. Department of Applied Chemistry, Faculty of Engineering, Chiba Institute of Technology, 2-17-1, Tsudanuma, Narashino, Chiba, 275-0016, Japan

    Mizuki Uzaki & Mitsuhiro Shibata

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  1. Mizuki Uzaki
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Contributions

All authors contributed to the study conception and design. Material preparation, data collection and analysis were performed by [Mizuki Uzaki]. The first draft of the manuscript was written by [Mitsuhiro Shibata]. All authors commented on previous versions of the manuscript. All authors read and approved the final manuscript.

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Correspondence to Mitsuhiro Shibata.

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Uzaki, M., Shibata, M. Preparation and properties of self-healing tung oil-based polymer networks driven by thermo-reversible Diels–Alder reaction. J Polym Res 29, 453 (2022). https://doi.org/10.1007/s10965-022-03303-z

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